Tips For Wearing A Hat

Wearing a hat has always been one of my favorite styling tricks. They keep you warmer in the winter, they provide some shade in the summer, and they cover troublesome hair. I own fedoras, Panamas, roll brim, straw, and felt ones but no ball caps, cloches, boaters, buckets, or beanies. Keep reading to learn why.

A hat makes a bold statement, so I keep the neckline open and never wear a necklace with a hat. I wear earrings mostly to cover the hole in my ears, never large eye-catching ones with a hat. Too many accessories always take a look in the wrong direction.

We visited First Watch on Sunday. It is a delightful daytime cafe serving fresh, healthy options for breakfast or lunch only.

I had the Frittata Rustica, a classic Italian-style omelet with kale, house-roasted Crimini mushrooms, onions, and tomatoes topped with Mozzarella Parmesan cheese—served with ciabatta toast and a salad. It was excellent!

Mr. Mickey had the Floridan French Toast made from thick-cut brioche with wheat germ and powdered cinnamon sugar, covered with fresh banana, kiwi, and seasonal berries.

My super casual and comfortable look included a fedora style hat from J.Jill. The relaxed cotton shirt is from Everlane. I did not tuck in any part of the shirt since I am wearing pull-on style ankle jeans from Liverpool Jeans Co. The tote bag is old. The Born sandals are from last year.

Hats with a brim that is not too wide and a crown that does not rest on the top of my head to flatten my hair are my best choice. I need some height at the crown, be it a hat or a hairstyle. I never repeat the roundish shape of my face in accessories, collars, or hairstyles.

If you have followed my journey for a while, you know that I am not an expert on anything. I do read a lot and enjoy doing research more than most people. I share what I learn to help you use my examples to figure out what works best for you. Looking and feeling your best is the first step to enjoying a full and healthy second fifty years with confidence. I hope you have a delightful weekend!

  1. Hats… of my big dilemmas. I’m short (5’1”) and fluffy. I have a very small head and hats make me feel like I look like a mushroom. I would LOVE to be able to pull off wearing a hat. Advice? Tips?

    1. There are now some popular styles which have a very narrow brim. Try one of those on in front of a full-length mirror. That style might be in better proportion for you.

  2. Susan, this close analysis of hat shapes in relation to face shapes is wonderful and helpful. I can appreciate your reason for not wearing a ball cap, and I’m adding one of my own, which is highly opinionated: I think ball caps are among the ugliest hats ever invented. Fine for ball players while they are playing, awful for everyone else. I simply cannot comprehend why the craze for them persists. There! I’ve gotten that off my chest! Thank you for all your useful remarks on shapes and styles of clothing and accessories, (always offered in a more courteous tone than I have used for this rant about ball caps). You have already improved my small wardrobe and my attention to how I present myself even when going out on errands in my very small town.

  3. Lovely outlook to wearing hats. I am with you Susan, in that the style of hat should complement the shape of our face. My problem is that I have a small head for hats, and children’s sizes just look silly – so the search goes on. Would it not be great if ladies started wearing hats regularly àgain?
    The breakfasts look amazing. Thank you for sharing. Have a great weekend both of you.

  4. Mr. Mickey’s French toast looks scrumptious. I love it made with brioche bread. I’ve never worn hats but as my skin is aging along with the rest of me, I’m beginning to think they have a purpose. Thanks for the primer.

  5. Susan,

    I get really bad “hat hair” when I wear a hat. I was just wondering – did you leave your hat on when you ate in the restaurant, or did you take it off?

    1. Take your fashion hat off only if it blocks someone’s view, such as at a wedding or in a theater. Do not wear a hat indoors at work.
      Only remove unisex hats, such as baseball caps when you go indoors.

  6. Thanks for your post. I love the Belmar hat!
    I noticed that the images of the hats you like are all summer/warm weather hats. What do you recommend for winter/cold weather hats for round faces?

    I enjoy your blog which has been so helpful.


  7. I love this casual outfit on you, Susan. You look well put together and yet comfortable. Have a great weekend!

  8. I would love to see a winter hat tutorial. Where I live, winter hats must cover ears snugly and protect from frostbite. Do I chose a slouchy hat, a toque…? Style goes out the window at times like these.

  9. I love this look, Susan. Thank you for including a site to order the tote. It’s on sale and with in-store pick up I avoided shipping. You’re so great!

  10. How do you keep,from getting hathair in warm weather. With our heat an h7midity in Southeast Louisiana, my hair always turns into a flat gooey mess if I wear a hat in summer. I love them but they don’t love me.

  11. Last year i bought a man’s straw fedora for my husband, but it was too small. I’ve been wearing it and have gotten many compliments…especially from other men. It’s a little large on me, which means I don’t get bad hat hair. I love it!

  12. Your advice has been so helpful and I look forward to your daily posts. I have purchased several scarves from your site and one of the Shapeez. I enjoy your adventures with Mr Mickey. You make a beautiful couple. You are loving life!

  13. I have never felt like I looked even passable in a hat, but now I’m wondering if I have just not tried the best style for my round face. As always, Susan, your advice has inspired me.

  14. I am always hesident about wearing a hat. I too am 5’1” and had read years ago that hats can actually make us (petite) appear shorter. I believe this can be the case because I have noticed how certain hats on small women do make them seem less tall and top heavy so to speak…..out of proportion. I would appreciate your take on this because you are so very savvy on such fashion details.

  15. Interesting and helpful post! I always enjoy your arrival in my inbox and appreciate the thought and work that you (and Mr Mickey) put into all your posts.

    I love hats but I wear glasses and felt that they detracted from the look, whereas sunglasses with a hat look OK. Strange! I solved the problem by getting a slightly blue tint to the lenses of my ordinary glasses. I can’t explain why but it makes such a difference.

    Like you, I look better in a hat with a brim. When it rains (most of the time in the UK!) I wear a waterproof leather fedora with my trench coat and it looks great – better than a leave-it-behind umbrella.

  16. I love your look, youthful, sportive, just great ……..thanks for the tips. Have a great weekend.
    The hat is super.

  17. Just wish hats came in a larger size to accommodate those of us who have lots of hair and a large head. There are a few, but not many. Ughhhh!

  18. I also love hats and wear one almost daily. Love your hat and again as usual the food looks yummy too. I especially like Mr. Mickey ‘s.

  19. Your pants are so cute on you! Do you order your regular size in this brand? The Liverpool Co. pictures make the jeans look extremely clingy so I’m hesitant. Yours look perfect.

    1. The ankle style pants are the best option for my shape. I do not find those to fit as tight as they show in the photos, but the jeggings do fit tight on the leg.

  20. Really appreciate your styling tips. At 76 years old I’ve decided to get more style in my clothing choices.
    I still have my natural brown hair which helps me look younger than I am from what people tell me.

  21. Susan, I moved from NY to the desert in Southern California in June. Talk about hot! Whew! I have enjoyed pulling out the hats I own plus shopping for some new ones. I have a very square face so I look to soften the angles. Hats I wore 10 years ago are not necessarily working. I own a very expensive Kaminski straw I bought in Annapolis while my son was at USNA. Since I don’t want to part with it I have been playing with the brim and some fun trim to replace the very dated grosgrain ribbon. I do wear a ball cap on the golf course but I have discovered some very long visors that don’t crush my hair & keep my head cooler. Also, Wallaroo makes some neat styles that are crushable for traveling. Enjoy your blog! Thanks for the inspiration!

    1. I have gray and black, or tan felt hats in the fedora style or a packable roll brim type. Since I have a fleshy roundish face, I look better in a hat with a high crown. (No toboggans or ball caps for the same reason.)

  22. This was very interesting, thanks. As for myself, I love hats…always have. I’m tall and slender. Right now my hair is quite short( poor choice) and just starting to get decent bangs again. I live in a small country western community with lots of farm land, farmers & cowboys and rodeos. As you can guess I wear cowboy hats from fall through winter. But I want to expand as a 69 yr old boho/hippie chick might. I like floppies, big/small brim, but I am wanting to try a flat brimmed hat. At the stores they are always too big for my head therefore sitting on the top of my head. I don’t like that. Any ideas about material…straw, cloth?
    Thanks for allowing me ask my questions. I enjoyed the site.

    1. Look at men’s Stenton’s. Straw or felt, they might fit you if as you say they sit on top of your head. Otherwise, look for small women’s hats and if they are still too small add a terry band to the inside. I found one example here of a hat you might be able to wear.

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I share tips and inspiration for using what you already have in contemporary ways. Defining words include effortless, classic, refined, discreet, and elegant. My style is chic, minimal, and timeless with a bit of edge.